CN103937283B - A kind of modified anthraquinone stain - Google Patents
A kind of modified anthraquinone stain Download PDFInfo
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- CN103937283B CN103937283B CN201310017428.2A CN201310017428A CN103937283B CN 103937283 B CN103937283 B CN 103937283B CN 201310017428 A CN201310017428 A CN 201310017428A CN 103937283 B CN103937283 B CN 103937283B
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- 0 *(c1ccccc1-1)c2ccc-3c4c2c-1ccc4Oc1c-3cccc1 Chemical compound *(c1ccccc1-1)c2ccc-3c4c2c-1ccc4Oc1c-3cccc1 0.000 description 2
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Abstract
A kind of modified anthraquinone stain, is in the molecular structure introduce amino or substituted-amino or piperidyl and water soluble group sulfonic group for parent by modified with water-insoluble anthraquinone dye.The structural formula of described modified anthraquinone substance is (1):A kind of modified anthraquinone stain provided by the invention, have that bright in color light, strong coloring force, dye uptake are high, compatibility is good each other, paper pulp painted after chroma in waste water low, dissolubility is high, good stability, the features such as not stratified not precipitation, reduce the use of color fixing agent in traditional dyeing and finishing process, reduce the impact on environment in dyeing process, and be prone to industrialized production, make the cost of papermaking and paper printing and dyeing be substantially reduced.
Description
Technical field
The present invention relates to a kind of modified anthraquinone stain, specifically, relate to a kind of water-insoluble anthraquinone dye and introduce amino or substituted-amino or piperidines amido and water soluble group sulfonic group in the molecular structure by modified, modified stain is made to have the features such as dissolubility height, good stability, not stratified not precipitation, not only reduce the use of color fixing agent in traditional dyeing and finishing process, reduce the impact on environment in dyeing process, and it is prone to industrialized production, make the cost of papermaking and paper printing and dyeing be substantially reduced.
Background technology
Direct dyes or reactive dye are wide in variety, chromatograph is complete, bright in colour, cheap, it is prone to colorant match, dyeing or printing method are easy, but maximum shortcoming to be the dyefastness major part of this kind of dyestuff good all not, degree of fixation is low, against weather is poor, easily decompose under the effect of external environment, cause that pollutant fades etc., affect the dyeability of these dyestuffs.For the defect that dyefastness is poor, people have done many reforms, for instance adopt chemical drugs, and the cloth catching color is carried out post processing, improve the washable and light fastness of painting cloth；Also have and adopt novel interlinkage color fixing agent to improve the post processing fastness of dyed fabric.In addition, it has been found that with have developed some reactive monoazo dyestuffs kinds, such as direct fast dye and direct copper dye etc..At present, to the light resistance and the wet colour fastness that how to improve direct dyes or reactive dye, also among further exploring.
The present invention is aiming at drawbacks described above, on the basis of original water-insoluble anthraquinone dye, is developed a kind of water-soluble dye by modified introducing amino or substituted-amino or piperidyl and water soluble group sulfonic group.
Summary of the invention
It is an object of the invention to provide a kind of modified anthraquinone stain, have that bright in color light, strong coloring force, dye uptake are high, compatibility is good each other, paper pulp painted after chroma in waste water low, dissolubility is high, good stability, the features such as not stratified not precipitation, reduce the use of color fixing agent in traditional dyeing and finishing process, reduce the impact on environment in dyeing process, and be prone to industrialized production, make the cost of papermaking and paper printing and dyeing be substantially reduced.
In order to achieve the above object, the invention provides a kind of modified anthraquinone stain.This stain is the dye matrix with some water-insoluble dye (such as solvent orange 63 etc.) for synthesis, and first chlorosulfonation introduces sulfonic group, imports amino or substituted-amino or piperidines amido again through aminolysis and obtain in parent.
As the anthraquinone stain that the present invention modifiies, there is below formula (1):
In formula, Pc represents that being selected from the Anthraquinones pigment being insoluble in water is dye matrix；
M is alkali metal cation or hydrogen；
R can be hydrogen, unsubstituted C1～C4 alkyl or alkoxyl, hydroxyl, halogen, sulfonic group；Can be maybe alkyl or the alkoxyl of the C1～C4 of hydroxyl, halogen, sulfonic group replacement；It can be maybe substituted or unsubstituted piperidyl；
M and n is natural number, and particularly suitable m is the natural number between 1-16, and n is the natural number between 0-2.
Described water-insoluble pigment is solvent orange 63 or solvent orange 35 or solvent orange 86.
Modified anthraquinone stain shown in aforementioned formula of the present invention (1), dye matrix (such as anthraquinone dye) shown in composition Pc can be added sulfonating agent and carry out sulfonation, sulfonated bodies filter cake sulfonation obtained again adds different ammonia and carries out amination, make above-mentioned sulfonated bodies aminolysis become the compound containing amino or piperidines amido or replacement sulfonamido structure, namely obtain the anthraquinone stain that formula of the present invention (1) is modified.
In the method for the invention, sulfonation temperature is 25～200 DEG C, and best sulfonation temperature is 80～125 DEG C；Amination temperature is 20～110 DEG C, and optimum temperature is 40～105 DEG C.
Sulfonating agent can be selected for concentrated sulphuric acid or oleum, sulfur trioxide, chlorosulfonic acid, sulfur dioxide add the one in chlorine, sulfur dioxide oxygenation, sodium sulfite, thionyl chloride, it is preferable that chlorosulfonic acid or thionyl chloride.It is more preferably chlorosulfonic acid.
In sulfonation process, it is common that Organic substance is slowly added in chlorosulfonic acid, feed in raw material in turn and can produce more sulfone by-product.
For making reaction uniform, sulfonation process Nitrobenzol, ortho-nitrophenyl, o-nitroethylbenzene, o-dichlorohenzene or dichloromethane, sym-tetrachloroethane or tetrachloroethylene etc. make diluent.It is low that chlorosulfonation has reaction temperature, the advantage simultaneously carrying out sulfonation and chlorination, is suitable to be difficult to the occasion of sulfonation.
In the method for the present invention, when dye matrix A carries out sulfonation, the mol ratio between dye matrix A and chlorosulfonic acid is 1: 4～20 or more chlorosulfonic acid, the number of sulfonamide that the consumption of chlorosulfonic acid will directly affect in the dye structure obtained below.
The pH value of aminating process should be not less than 7.0；Aminating agent can use ammonia, substituted-amino (such as organic amine 3,3-dimethoxy Propanolamine, isopropanolamine, diethanolamine, monoethanolamine, dimerization ethanolamine etc.), 4-amino-2,2,6,6-tetramethylpiperidine etc..
In aforementioned formula (1), R1The sulfonic group number m contained in structure depends on the consumption of chlorosulfonic acid, is namely sulfonated the material ratio between thing and chlorosulfonic acid；And sulfonic number is by the number n of the amino generated when directly affecting amination or substituted-amino.Therefore, the structure of the final modification of and coloration agent prepared is played vital effect by the consumption of sulfonating agent chlorosulfonic acid.
Modified anthraquinone stain provided by the invention is a kind of dyestuff with good aqueous solubility, it is possible to for powdery or for be dissolved in the liquid of water or to be dissolved in the liquid of alcohols solvent, and powdery solid content soluble in water can reach 50%.This water-soluble dye can individually or with other dyestuff mixture use.Suitable in papermaking and paper coloring, and have that bright in color light, strong coloring force, dye uptake are high, compatibility is good each other, paper pulp painted after the feature such as chroma in waste water low, dissolubility is high, good stability, not stratified not precipitation, not only reduce the use of color fixing agent in traditional dyeing and finishing process, reduce the impact on environment in dyeing process, and it is prone to industrialized production, make the cost of papermaking and paper printing and dyeing be substantially reduced.
Modified anthraquinone stain provided by the invention, the industrial circle used or industry are colored paper and dye ink manufacture: in paper manufactures, be mainly used in the dyeing of the paper of the kinds such as art paper, LWC, newsprint, Bible paper, kraft liner, coated white paperboard, chipboard, cellophane, wrapping paper, bag kraft paper, toilet paper, facial tissue, diaper, medicated napkin, napkin, medicinal paper；The dye ink produced, is mainly used in ink-jet print system.
Figure of description
Fig. 1 is the infrared spectrum of the anthraquinone stain that embodiment 1 modifiies.
Detailed description of the invention
A kind of modified anthraquinone stain provided by the invention, its preparation method is as follows:
Step 1, use anthraquinone dye and chlorosulfonic acid prepare anthraquinone sulfonic acid chloride under reacting at 80～200 DEG C, suitably add thionyl chloride；
Step 2, being diluted in mixture of ice and water by anthraquinone chlorosulfonic acid mixture, then filter, the dilute hydrochloric acid ice water solution with 0.3%～0.7% washs, and obtains anthraquinone sulfonated bodies filter cake；
Step 3, anthraquinone sulfonated bodies filter cake being dissolved in frozen water, and different amine reacts 2 hours～8 hours, after having reacted in water, product acid adding precipitates out.
Below by specific embodiment, better illustrate modified anthraquinone stain provided by the invention.In the embodiment shown, except as otherwise noted, all of material is all by weight.
Embodiment 1
Reaction vessel adds 40 parts of chlorosulfonic acids, is slowly added into 20 parts of solvent orange 63s, control temperature when feeding intake between 25-40 DEG C.After adding, it is slowly ramped to 90 DEG C, at this temperature insulated and stirred 1h.After insulation terminates, more uniformly it is warmed up to 100～120 DEG C, is incubated 6 hours at 100～120 DEG C.Appropriate thionyl chloride is added in insulation after terminating, continue insulation 1.0h.It is subsequently poured in frozen water, is filtrated to get the anthraquinone sulfonic acid chloride that chlorosulfonic acid replaces, and washs with the dilute hydrochloric acid ice water solution of 0.5%.Chlorosulfonation thing filter cake is joined in 100 parts of water, is cooled to less than 20 DEG C, and regulate pH=7.5 with the aqueous solution of 3,3-dimethoxy Propanolamines, stirred below 2～4 hours at 20 DEG C.It is warmed up to 20～30 degree, adds 30% hydrochloric acid, then agitation and filtration, after filter cake dilute hydrochloric acid solution washs, be dried at 50～70 degree, obtain crude product.Remove inorganic salt by nanofiltration and evaporation and concentration, finally obtain (R1 and R2=-SO3(NH4)+) pure dye powder body, the anthraquinone stain that namely formula of the present invention (1) is modified.Its structural formula is expressed as follows:
This stain has carried out infrared analysis, and concrete spectrogram is shown in accompanying drawing 1.By spectrogram it can be seen that the gamut of infrared spectrum can be divided into 4000～1350cm-1With 1350～650cm-1Two regions.4000～1350cm-1Region is the absorption band produced by stretching vibration, and spectrum is relatively simple but has very strong characteristic, is called functional group region.At this region, 4000～2500cm-1There is the stretching vibration absorption band of functional group's O-H, N-H, C-H, S-H key that the hydrogen atom little with reduced mass combine high wave number one end；At 2500～1900cm-1There is three key that force constant is big in wave-number range；At 1900cm-1Following lower wave number end is the skeletal vibration of the stretching vibration of carbon-carbon double bond, C=O bond, carbon-to-nitrogen double bon, nitrogen oxygen double bond etc. and aromatic ring.
At 1350～650cm-1, there are the stretching vibration of C-O, C-X and the skeletal vibration of C-C in region, also has the absworption peak that the bending vibration that force constant is less produces, and therefore spectrum is extremely complex.The absorption position at Zhong Ge peak, this region is relatively big by the impact of overall molecule structure, and molecular structure is slightly different, absorbs and just has subtle difference.
Adsorption frequency is also produced impact by intramolecule structure.The electrical effects such as inductive effect, conjugation and dipole field effect can cause the change of the distribution of electronics in molecule, thus causing the change of chemical bond force constant and changing the characteristic frequency of group.The hydrogen bond impact on absorbing position is also very big, and O-H, N-H key of association is also all to the displacement of lower wave number direction, and this is the reason owing to hydrogen bond makes O-H, N-H key in molecule weaken.Association body is not single, has difformity and different size, is a mixture, therefore forms a wider band, is substantially combined by the absworption peak of different hydrogen bonds.
Can contrasting from the book information etc. of above-mentioned infrared spectrum 1 and Spectrum Analysis and find out, sample is at 3416cm-1There is a very wide characteristic absorption at wave number place, therefore, can conclude that in this sample containing N-H key and sulfone, integrates and be sulfoamido.Demonstrate that what obtain by method described in this patent is the modified product containing amino or substituted-amino (such as sulfoamido).
Embodiment 2
Reaction vessel adds 80 parts of chlorosulfonic acids, is slowly added into 20 parts of solvent orange 63s, control temperature when feeding intake between 25-40 DEG C.After adding, it is slowly ramped to 90 DEG C, at this temperature insulated and stirred 1h.After insulation terminates, more uniformly it is warmed up to 100～120 DEG C, is incubated 6 hours at 100～120 DEG C.Appropriate thionyl chloride is added in insulation after terminating, continue insulation 1.0h.It is subsequently poured in frozen water, is filtrated to get the anthraquinone sulfonic acid chloride that chlorosulfonic acid replaces, and washs with the dilute hydrochloric acid ice water solution of 0.5%.Chlorosulfonation thing filter cake is joined in 100 parts of water, is cooled to less than 20 DEG C, and regulate pH=7.5 with the aqueous solution of isopropanolamine, stirred below 2～4 hours at 20 DEG C.It is warmed up to 20～30 degree, adds 30% hydrochloric acid, then agitation and filtration, after filter cake dilute hydrochloric acid solution washs, be dried at 50～70 degree, obtain crude product.Remove inorganic salt by nanofiltration and evaporation and concentration, finally obtain (R1 and R2=-SO3(NH4)+) pure dye powder body, the anthraquinone stain that namely formula of the present invention (1) is modified.Its structural formula is expressed as follows:
Embodiment 3
Reaction vessel adds 60 parts of chlorosulfonic acids, is slowly added into 20 parts of solvent orange 63s, control temperature when feeding intake between 25-40 DEG C.After adding, it is slowly ramped to 90 DEG C, at this temperature insulated and stirred 1h.After insulation terminates, more uniformly it is warmed up to 100～120 DEG C, is incubated 6 hours at 100～120 DEG C.Appropriate thionyl chloride is added in insulation after terminating, continue insulation 1.0h.It is subsequently poured in frozen water, is filtrated to get the anthraquinone sulfonic acid chloride that chlorosulfonic acid replaces, and washs with the dilute hydrochloric acid ice water solution of 0.5%.Chlorosulfonation thing filter cake is joined in 100 parts of water, is cooled to less than 20 DEG C, and regulate pH=7.5 with 4-amino-2,2,6,6-tetramethylpiperidine solution, stirred below 2～4 hours at 20 DEG C.It is warmed up to 20～30 degree, adds 30% hydrochloric acid, then agitation and filtration, after filter cake dilute hydrochloric acid solution washs, be dried at 50～70 degree, obtain crude product.Remove inorganic salt by nanofiltration and evaporation and concentration, finally obtain (R1 and R2=-SO3(NH4)+) pure dye powder body, the anthraquinone stain that namely formula of the present invention (1) is modified.Its structural formula is expressed as follows:
Embodiment 4
Reaction vessel adds 70 parts of chlorosulfonic acids, is slowly added into 20 portions of solvent oranges 35, control temperature when feeding intake between 25-40 DEG C.After adding, it is slowly ramped to 90 DEG C, at this temperature insulated and stirred 1h.After insulation terminates, more uniformly it is warmed up to 100～120 DEG C, is incubated 6 hours at 100～120 DEG C.Appropriate thionyl chloride is added in insulation after terminating, continue insulation 1.0h.It is subsequently poured in frozen water, is filtrated to get the anthraquinone sulfonic acid chloride that chlorosulfonic acid replaces, and washs with the dilute hydrochloric acid ice water solution of 0.5%.Chlorosulfonation thing filter cake is joined in 100 parts of ammonia, stirred below 2～4 hours at 20 DEG C.It is warmed up to 20～30 degree, adds 30% hydrochloric acid, then agitation and filtration, after filter cake dilute hydrochloric acid solution washs, be dried at 50～70 degree, obtain crude product.Remove inorganic salt by nanofiltration and evaporation and concentration, finally obtain (R1 and R2=-SO3(NH4)+) pure dye powder body, the anthraquinone stain that namely formula of the present invention (1) is modified.Its structural formula is expressed as follows:
Embodiment 5
Reaction vessel adds 65 parts of chlorosulfonic acids, is slowly added into 20 portions of solvent oranges 86, control temperature when feeding intake between 25-40 DEG C.After adding, it is slowly ramped to 90 DEG C, at this temperature insulated and stirred 1h.After insulation terminates, more uniformly it is warmed up to 100～120 DEG C, is incubated 6 hours at 100～120 DEG C.Appropriate thionyl chloride is added in insulation after terminating, continue insulation 1.0h.It is subsequently poured in frozen water, is filtrated to get the anthraquinone sulfonic acid chloride that chlorosulfonic acid replaces, and washs with the dilute hydrochloric acid ice water solution of 0.5%.Chlorosulfonation thing filter cake is joined in 100 parts of ammonia, stirred below 2～4 hours at 20 DEG C.It is warmed up to 20～30 degree, adds 30% hydrochloric acid, then agitation and filtration, after filter cake dilute hydrochloric acid solution washs, be dried at 50～70 degree, obtain crude product.Remove inorganic salt by nanofiltration and evaporation and concentration, finally obtain (R1 and R2=-SO3(NH4)+) pure dye powder body, the anthraquinone stain that namely formula of the present invention (1) is modified.Its structural formula is expressed as follows:
Embodiment 6
Any one product 50 parts of gained, azo metal complex 20～30 parts, acetic acid sodium salt 15～20 parts and acetoglyceride 5 parts in 100 parts of water, embodiments 1～5 is added in reactor.Being configured to uniform solution after being sufficiently stirred for for contaminating paper colour examining light, concrete data are as follows:
Symbolic significance in upper table illustrates as follows:
DL: luminosity equation, generally requires just to compare its coloured light under waiting deep feeling condition when DL < 0.5 poor；
Da and Db represents the change of tone, and+Da represents partially red compared with standard specimen, and-Da represents partially green compared with standard specimen；+ Db represents partially yellow, and-Db represents partially blue；
DC: gorgeous degree is poor, illustrates more bright-coloured than standard specimen more than zero, otherwise illustrates darker than standard specimen；
DE: the system aberration of total color difference, standard specimen and sample, DEMore big, illustrate that the aberration of sample differs more big with standard specimen；
DH: hue difference, by red → yellow → green → blue → red direction change during more than zero, by above-mentioned inverse change during less than zero.
Can contrasting from the data above and find out, add azo metal complex, the anthraquinone colorant mixture bright in color light degree of acetic acid sodium salt and acetoglyceride post-modification is apparently higher than single product, and its dye uptake on paper is also high by about 8%.
Claims (8)
1. the mixture of a modified anthraquinone stain, it is characterised in that it comprises the modified anthraquinone stain of 50%w/w, the azo metal complex of 20-30%w/w, the acetic acid sodium salt of 15-20%w/w and the acetoglyceride of 5%w/w；Wherein, the described modified anthraquinone stain dye matrix with water-insoluble pigment for synthesis, first chlorosulfonation introduces sulfonic group, in parent, amino or substituted-amino or 2,2,6 are imported again through aminolysis, 6-tetramethyl piperidine amido and obtain, the structural formula of described modified anthraquinone stain is:
In formula, Pc represents that being selected from the Anthraquinones pigment being insoluble in water is dye matrix；
M is alkali metal cation or hydrogen；
R can be hydrogen, unsubstituted C1～C4 alkyl or alkoxyl, hydroxyl, halogen, sulfonic group；Can be maybe alkyl or the alkoxyl of the C1～C4 of hydroxyl, halogen, sulfonic group replacement；Can be maybe 2,2,6,6-tetramethyl-piperidyl,
M is the natural number between 1-16, and n is the natural number between 0-2；
Described water-insoluble pigment is solvent orange 63 or solvent orange 35 or solvent orange 86.
2. the mixture of modified anthraquinone stain as claimed in claim 1, it is characterised in that described azo metal complex is azo copper complex or azo iron complex.
3. modifiy the mixture of anthraquinone stain as claimed in claim 1, it is characterized in that, the preparation method of wherein said modified anthraquinone stain is: the dye matrix constituted shown in Pc addition sulfonating agent is carried out sulfonation, again sulfonated bodies filter cake is carried out amination, sulfonated bodies aminolysis is made to become the compound containing sulfonamido structure, ammonia is used during aminolysis, organic amine 3, 3-dimethoxy Propanolamine, isopropanolamine, diethanolamine, monoethanolamine, dimerization ethanolamine or 4-amino-2, 2, 6, 6-tetramethyl piperidine carries out amination, wherein sulfonating agent is concentrated sulphuric acid or oleum, sulfur trioxide, chlorosulfonic acid, sulfur dioxide adds chlorine, sulfur dioxide oxygenation, one in sodium sulfite or thionyl chloride.
4. the mixture of modified anthraquinone stain as claimed in claim 3, it is characterized in that, described sulfonating agent is chlorosulfonic acid, when the chlorosulfonation thing that chlorosulfuric acid obtains carries out aminolysis, pH value with reactant liquor is as the criterion by the consumption of different amine, and the pH value of amination is not less than 7.0.
5. the mixture of anthraquinone stain as claimed in claim 1 modified, it is characterised in that wherein said modified anthraquinone stain is be dissolved in the liquid of water or be dissolved in the liquid of alcohols solvent, individually or use together with other dyestuff mixture.
6. the purposes of the mixture of modified anthraquinone stain as claimed in claim 1, it is characterised in that it is for colored paper and dye ink manufacturing.
7. the purposes of the mixture of modified anthraquinone stain as claimed in claim 1, it is characterized in that, it is applied to the dyeing of paper of art paper, LWC, newsprint, Bible paper, kraft liner, coated white paperboard, chipboard, cellophane, wrapping paper, bag kraft paper, toilet paper, diaper, medicated napkin or medicinal paper.
8. the purposes of the mixture of modified anthraquinone stain as claimed in claim 1, it is characterised in that for producing the dye ink that ink-jet print system uses.
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| CN108558712A (en) * | 2018-06-20 | 2018-09-21 | 新乡市锦源化工有限公司 | It is a kind of using antifebrin as the method and P-aminobenzene-sulfonamide of Material synthesis high-purity P-aminobenzene-sulfonamide |
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| CN1121941A (en) * | 1994-05-17 | 1996-05-08 | 赫彻斯特股份公司 | Water-soluble anthraquinone compounds, preparation thereof and use thereof as dyes |
| CN1234054A (en) * | 1996-09-03 | 1999-11-03 | 伊斯曼化学公司 | Anthraquinone polysulfonamide colorants |
| CN1995150A (en) * | 2006-12-21 | 2007-07-11 | 大连理工大学 | Slightly water-soluble sulfonamide type dye for dying hydrophobic fiber and its preparation |
| CN101864188A (en) * | 2009-04-17 | 2010-10-20 | 上海汇友精密化学品有限公司 | Sunproof water-soluble dye, method for preparing same and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010075780A1 (en) * | 2008-12-31 | 2010-07-08 | 大连理工大学 | A weather resistance black dye and its preparation and use |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1121941A (en) * | 1994-05-17 | 1996-05-08 | 赫彻斯特股份公司 | Water-soluble anthraquinone compounds, preparation thereof and use thereof as dyes |
| CN1234054A (en) * | 1996-09-03 | 1999-11-03 | 伊斯曼化学公司 | Anthraquinone polysulfonamide colorants |
| CN1995150A (en) * | 2006-12-21 | 2007-07-11 | 大连理工大学 | Slightly water-soluble sulfonamide type dye for dying hydrophobic fiber and its preparation |
| CN101864188A (en) * | 2009-04-17 | 2010-10-20 | 上海汇友精密化学品有限公司 | Sunproof water-soluble dye, method for preparing same and application thereof |
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